This is a fun topic to think about. Off the cuff I'd go with a Seven Mudhoney SL with rack and fender mounts, painted to look like a POS, Hollowgram SRM, debadged Force, Alchemy/CX Ray/Stan's 340, locking bolt on skewers. That should cover summer road riding, fenders and studded tires in the winter, and with most of the logos removed hopefully it'd be low profile enough to lock up at the store.

I'm actually in the process of building my dream bike. It is costly, but the "dream" is fulfilled not just by buying top shelf parts. I could spec a bike that costs $25k, but it may not be very tasteful or it may reflect strongly on the fashion of the day and lack a timeless quality that I want in a bike I'll ride for decades to come. To that end, my dream bike is shaping up to be:

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